Manufacture of binaphthylenedioxide-quinone



Patente 4, 1930 LUDWIG ZEE, OF 'WIESDORF-ON-THE-BHINE, GERMANY, ASSIGNOR TO GENERAL ANILINE WORKS, INC., NEW YORK, N. Y., A CORPORATION; OLE-DELAWARE MANUFACTURE OF BINAPHTHYLENEDIOXIDE-QUINONE No Drawing. Application filed October 4, 1928, Serial No. 310,443, and in Germany October 13, 192 7.

two 0x gen atoms into the binaphthylene o dioxide and the temperatures to be used vary between about 2050 C. When working in this manner a binaphthylene dioxide quinone of the probable formula is obtainable difi'ering from other binaphthylene dioxidequinones heretofore known especially by its nearly insolubility in the usual organic solvents.

The following example illustrates my mvention without limiting it thereto, the parts being by weight:

E mampZe.-15 parts of fine divided binaphthylene dioxide are suspended in 400 parts of sulfuric acid of about 25% strength. To this mixture a concentrated aqueous solution of about 30 parts oi chromic acid is allowed to drop in, while maintaining the temperature at about 4050 C. As soon as all of the binaphthylene dioxide has disappeared the reaction mass is cooled and filtered. The residue is washed with water until neutral, dried and extracted with boiling pyridine until all impurities are removed. The remaining. binaphthylene dioxide qumone forms a reddish brown powder nearly 1nsoluble in pyridine and the usual organic solvents. From large quantities of boiling aniline it can be obtained in a small amount in form of brown needles which dissolve in concentrated sulfuric acid with a reddish blue coloration and strong reddish violet fluorescence. When treating it with sodium hydrosulfite in alkaline solution a yellow vat is obtained, from which the sodium salt of the leuco binaphthylene dioxide can be obtained in form of yellow six edge-d leaflets, and from which vat cotton is dyed clear brown shades of good fastness properties.

' I claim I 1. Process which comprises reacting upon finely divided binaphthylene dioxide suspended in water with chromic acid at a temperature between about 20-50 C.

2. Process which comprises recting upon finely divided binaphthylene dioxide suspended in water with an excess of chromic acid, and with the addition of sulfuric acid at a temperature between about 20-50 C.

3. Process which comprises reacting upon 15 parts of finely divided binaphthylene dioxide suspended in sulfuric acid of about 25% strength with a concentrated aqueous solution of 30 parts of chromic acid at a temperature of about 40-50" C.

4 The compound of the probable-formula said compound forming a reddish brown powder nearly insoluble in the usual organic solvents, obtainable from large quantities of boiling aniline in form of yellow needles, dis- 99 solving in concentrated sulfuric acid with a reddish-blue coloration and with strong reddish-violet fluorescence, dyeing cotton from a hydrosulfite vat clear brown shades of good fastness properties.

In testimony whereof I have hereunto set m hand.

- y LUDWIG ZEH, [L.S.]

cc rtr chm or cohecrtom.

- Fotent No. l,749,0id. Gronted March 4, 1930, .to

worm es.

it is hereby certified that error gppesrs in the printed specification'of the. above nred potent correction as ioilows: 4 Page 1, line 7; after the word "scid"ood hetero the period insert the words "preierabiy with the addition oi'oulturie oeid"; end that the said Letters Pateri't should be read with this correction therein that the some may conform to the record of the case in the Patent Office.

Sim t seal that 8th th ti April, A. o. 1930..

' M. E. Moore, (%ci) Acting with of Potwts. 

